136561-53-0

Basic information

• Product Name: (2R,3S)-3-Phenylisoserine
• Synonyms: H-ISE(3-PHENYL)-OH;3-(2R,3S)-PHENYLISOSERINE;(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanic acid;(2R,3S)-3-AMINO-2-HYDROXY-3-PHENYL-PROPANOIC ACID;(2R,3S)-3-PHENYLISOSERINE 99%;(2R,3S)-3-Phenylisoserine;(2R,3S)-2-hydroxy-3-aMino-3-phenylpropionic acid;3-(2R,3S)-Phenylisoserine≥ 98% (NMR)
• CAS NO: 136561-53-0
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Mol File: 136561-53-0.mol

Chemical Properties

• Boiling Point: 360.6 °C at 760 mmHg
• Flash Point: 171.9 °C
• Appearance: /
• Density: 1.335
• Vapor Pressure: 7.87E-06mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: 2-8°C
• PKA: 2.56±0.27(Predicted)
• CAS DataBase Reference: (2R,3S)-3-Phenylisoserine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-Phenylisoserine(136561-53-0)
• EPA Substance Registry System: (2R,3S)-3-Phenylisoserine(136561-53-0)

Safety Data

• Hazardous Substances Data: 136561-53-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Intermediate for the synthesis of taxol.

InChI:InChI=1/C9H13NO2/c10-9(8(12)6-11)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6,10H2/t8-,9-/m0/s1

Upstream product

• 141901-21-5 (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide 
• 133066-59-8 (±)-cis-3-acetyloxy-4-phenylazetidin-2-one 
• 103-26-4 Methyl cinnamate 
• 438566-45-1 (3R,4S)-3-benzyloxy-1-[(2S)-2-(1-ethyl-1-methoxypropyl)pyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 438566-59-7 (3R,4S)-cis-3-benzyloxy-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 130632-19-8 (-)-(3R,4S)-3-Benzyloxy-4-phenylazetidin-2-one 
• 479078-61-0 (4S,5R)-2-Oxo-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 
• 60512-85-8 (E)-isopropyl cinnamate 
• 195624-97-6 (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester 
• 145514-62-1 RPR 130523 
• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 176298-46-7 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 151310-06-4 2-hydroxy-3-amino-3-phenylpropionamide 

Downstream Products

• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 532393-27-4 (2R,3S)-methyl 3-acetamido-2-acetyloxy-3-phenylpropanoate 
• 158225-44-6 Methyl N-acetyl-3-phenylisoserine 
• 100-52-7 benzaldehyde 
• 949023-16-9 (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid 

Relevant articles and documents

Utilization of (18-Crown-6)-2,3,11,12-tetracarboxylic Acid as a Chiral NMR Solvating Agent for Diamines and β-Amino Acids

The compound (18-crown-6)-2,3,11,12-tetracarboxylic acid was evaluated as a chiral nuclear magnetic resonance (NMR) solvating agent for a series of diamines and bicyclic β-amino acids. The amine must be protonated for strong association with the crown ether. An advantage of (18-crown-6)-2,3,11,12-tetracarboxylic acid over many other crown ethers is that it undergoes a neutralization reaction with neutral amines to form the protonated species needed for binding. Twelve primary diamines in neutral and protonated forms were evaluated. Diamines with aryl and aliphatic groups were examined. Some are atropisomers with equivalent amine groups. Others have two nonequivalent amine groups. Association equilibria for these systems are complex, given the potential formation of 2:1, 1:1, and 1:2 crown-amine complexes and given the various charged species in solution for mixtures of the crown ether with the neutral amine. The crown ether produced enantiomeric differentiation in the 1H NMR spectrum of one or more resonances for every diamine substrate. Also, a series of five bicyclic β-amino acids were examined and (18-crown-6)-2,3,11,12-tetracarboxylic acid caused enantiomeric differentiation in the 1H NMR spectrum of three or more resonances of each compound. Chirality 27:708-715, 2015.

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

Enantioselective hydrolysis of 3,4-disubstituted β-lactams. An efficient enzymatic method for the preparation of a key Taxol side-chain intermediate

3,4-Disubstituted β-lactams 3-benzyloxy-4-(4-chlorophenyl)azetidin-2-one [(3S?,4R?)-(±)-1], 3-benzyloxy-4-phenylazetidin-2-one [(3S?,4R?)-(±)-2] and 4-(4-chlorophenyl)-3-phenoxyazetidin-2-one [(3S?,4R?)-(±)-3] were resolved through immobilized CAL-B-catalysed ring-cleavage reactions. Excellent enantioselectivities (E > 200) were obtained for (3S?,4R?)-(±)-1 and (3S?,4R?)-(±)-2 when the reactions were performed with added H2O as nucleophile in tert-butyl methyl ether at 70 °C, whereas only moderate E (12) was achieved for (3S?,4R?)-(±)-3 under the same conditions but in diisopropyl ether. The resulting ring-opened β-amino acids [(2R,3S)-4 (ee > 98%), (2R,3S)-5 (ee > 98%) and (2R,3S)-6 (ee = 50%)] and the unreacted β-lactams [(3S,4R)-1-3] (ee > 98%) could be easily separated.

An investigation of nitrile transforming enzymes in the chemo-enzymatic synthesis of the taxol sidechain

Paclitaxel (taxol) is an antimicrotubule agent widely used in the treatment of cancer. Taxol is prepared in a semisynthetic route by coupling the N-benzoyl-(2R,3S)-3-phenylisoserine sidechain to the baccatin III core structure. Precursors of the taxol sidechain have previously been prepared in chemoenzymatic approaches using acylases, lipases, and reductases, mostly featuring the enantioselective, enzymatic step early in the reaction pathway. Here, nitrile hydrolysing enzymes, namely nitrile hydratases and nitrilases, are investigated for the enzymatic hydrolysis of two different sidechain precursors. Both sidechain precursors, an openchain α-hydroxy-β-amino nitrile and a cyanodihydrooxazole, are suitable for coupling to baccatin III directly after the enzymatic step. An extensive set of nitrilases and nitrile hydratases was screened towards their activity and selectivity in the hydrolysis of two taxol sidechain precursors and their epimers. A number of nitrilases and nitrile hydratases converted both sidechain precursors and their epimers.

New enzymatic two-step cascade reaction for the preparation of a key intermediate for the taxol side-chain

Enzymatic strategies are reported for the synthesis of (2R, 3S)-3-amino-2-hydroxy-3-phenylpropionic acid (ee > 98%), a key intermediate of the side-chain of Taxolby enzymatic hydrolysis in organic media. The new enzymatic cascade reaction, which took place through Candida antarctica lipase B-catalysed deacylation followed by lactam ring-opening of racemic cis-3-acetoxy-4-phenylazetidin-2-one with H2O in iPr2O at: 60 °C, resulted in two different enantiopure products (ee ≥ 98%), one of them being the desired key intermediate for the side-chain of Taxol.

A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain

Burkholderia cepacia lipase PS-IM catalysed the hydrolysis of racemic ethyl 3-amino-3-phenyl-2-hydroxypropionate with excellent enantioselectivity (E >200), when the reaction was performed with added H2O as a nucleophile, in iPr2O, at 50 °C. The hydrolysis of the less reactive enantiomeric ethyl 3-amino-3-phenyl-2-hydroxypropionate with 18% HCl afforded the corresponding enantiomerically pure (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid hydrochloride, a key intermediate for the Taxol side chain.

Tachysan useful for synthesizing method for producing compd. homochiral

A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer:wherein P1 is H or a hydroxyl protecting group, R1 is H, an alkyl group, an olefinic group or an aromatic group, and R2 is H or R3CO, where R3 is an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group or an O-aromatic group, provided that Ris not H when Ris Ph and Pis H. The method includes passing the solution through a chromatographic stationary phase, such as S,S Whelk-O, that has a greater affinity for one of the target isomer and an optical isomer thereof. A portion of the solution with the target isomer is then collected. The solution may be a racemic mixture of (±)-N-CBZ-3-phenylisoserine ethyl ester.

The design and synthesis of guanosine compounds with in vitro activity against the colon cancer cell line SW480: Non-taxane derived mimics of taxol?

In the course of our investigation into the use of taxol as a lead compound to design new molecules with anti-cancer activity, we have synthesized four compounds based on protected guanosine coupled to taxol isoserine side-chain analogues. These analogues show in vitro anti-cancer activity against the colon cancer cell line SW480 that their constituent parts do not.

Chiral resolution method for producing compounds useful in the synthesis of taxanes

A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer: wherein P1 is H or a hydroxyl protecting group, R1 is H, an alkyl group, an olefinic group or an aromatic group, and R2 is H or R3CO, where R3 is an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group or an O-aromatic group, provided that R1 is not H when R3 is Ph and P1 is H. The method includes passing the solution through a chromatographic stationary phase, such as S,S Whelk-O, that has a greater affinity for one of the target isomer and an optical isomer thereof. A portion of the solution with the target isomer is then collected. The solution may be a racemic mixture of (±)-N-CBZ-3-phenylisoserine ethyl ester.

First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines

α-Hydroxy-β-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.